


Caribbean Cruising

by Follow2thedark



Category: Supernatural
Genre: Alternate Universe - Human, Castiel is Older Than Dean Winchester, Cruising, M/M, Other Additional Tags to Be Added, Shy Dean Winchester, Smart Dean Winchester, Summer Vacation, Teen Dean Winchester, Underage Drinking, Virgin Dean Winchester
Language: English
Status: In-Progress
Published: 2019-03-12
Updated: 2019-03-11
Packaged: 2019-11-15 10:50:19
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,366
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18072005
Author URL: https://archiveofourown.org/users/Follow2thedark/pseuds/Follow2thedark
Summary: On a Caribbean cruise, eighteen-year old Dean Winchester's to-do list includes having a one night stand, but when his wealthy new stepfather introduces his gorgeous godson as his traveling buddy, things become complicated.Based on book by the same name by Rachel Hawthorne





	Caribbean Cruising

"I can't believe it! Everything is totally amazing!"  
  
  
Dean couldn't believe it either as he and Charlie Bradbury gazed around the atrium of  _The Enchantment_. The named suited this ship. Dean was definitely enchanted. It was huge and luxurious. Dean figured it would take all ten nights of the cruise simply to walk from one end of the ship to the other.

 "Come on," Dean said, nudging Charlie's arm. "Let's go check out my cabin."  
  
Charlie was Dean's best friend. Her fiery red hair matched her personality perfectly, and she was a lot of energy in a compact package. She had a difficult time keeping up when Dean was in a hurry like he was now. He just wanted to see everything as quickly as possible. There was so much to take in. His time there would be short, and he didn't want to waste a single minute.  
  
"Slow down, Dean," Charlie ordered. "Your cabin's not going anywhere."  
  
No, it wasn't, but he was anxious to see it, to get settled in. Still, he did slow down as they walked along a wide corridor, which closely resembled a boulevard. Stores and restaurants lined both sides. Plants, statuettes, artwork, festive lights, and a domed ceiling created an openness that Dean wasn't expecting within a ship. It was like touring a gigantic mall-one of Charlie's favorite places to drag Dean to after school. With so many people mingling around, it was like a bustling city floating on the ocean. Dean was a little overwhelmed by the crowds and the vastness of the ship.

 "It's just not fair that I have to work and can't go on this cruise with you," Charlie lamented.   
  
Those words had become Charlie's mantra ever since Dean told her that he was going on this trip.  
  
"I'd give anything if you could come Charles," Dean said.  
  
They'd shared everything since kindergarten. Dean couldn't imagine not sharing this too.  
  
"I know. You have to send me post cards from every port," she commanded.  
  
"Yes, my Queen," Dean joked.  
  
"And since you're so into making lists, I expect a report listing all the yummy details about every guy you meet."  
  
"I thought you'd want to hear about the ladies," Dean chuckled.  
  
"Ugh! Don't remind me! I'm telling you, this trip is wasted on you," Charlie nudged Dean's ribs playfully.  
  
Dean laughed. He was a little obsessed with lists. You couldn't tell by looking at him but he liked organization and had compiled several different list as soon as he found out he was going on a cruise-everything he needed to buy before he came onboard, all the items he needed to pack, and everything Dean planned to do while on this cruise.  
  
"Maybe I'll just send you a list of their names. I'm hoping there will be so many that I won't have room on the postcards to tell you about all of them."

"Ah, the student has surpassed the teacher." Charlie said with pride.

Dean snorted and glanced around the boulevard again. From the moment he'd checked in and they'd started their quick tour of the ship, he'd seen at least a dozen guys who he thought he'd like to get to know better. Each one was smiling, laughing or talking with someone.   
  
"I think it's romantic that Michael is going to marry your mom on a cruise ship," Charlie stated.   
  
"He's definitely gone all out." Dean mumbled.  
  
Michael Edlund was quiet and reserved, but when he spoke, people listened and did as he asked. Mostly because his name appeared on a famous list of the top one hundred wealthiest people in the world.  
  
Hence the cruise. A special honeymoon for him and his new bride-who just happened to be Dean's mom-and anyone else who wanted to tag along. Of which Dean was undeniably one.  
  
They say that most people are introduced by a friend to the person they'll marry. That's how Mary Winchester met Michael. She was attending a friend's funeral. Her friend had worked for Michael's company so Michael had gone to the funeral as well. He and Mary met, hit it off and now Dean's life was on the verge of changing forever in ways that he'd never really anticipated. And truthfully, it's something he'd been having a hard time comprehending. For as long as Dean could remember, it had always been just him and Mary. Now it would be Dean, Mary and Michael.  
  
Still, Michael was nice and Dean liked him. Dean thought he'd be good for his mom. Dean was heading off to the University of Texas in the fall, and he'd been a little worried about Mary dealing with the empty nest. So he was definitely in favor of her marrying Michael.  
  
Dean didn't think most cruise ships allowed wedding guests onboard, but Michael had made special arrangements so they could have their friends and family attend. Michael had reserved the top deck for the ceremony. At midnight they'd have the official bon voyage and prepare to leave port of Galveston. The guests would depart, and the ship would sail away into the night towards the Caribbean.  

"I can't believe you're going to  spend ten days on this ship! Did you see all those stores we just passed on the boulevard?" Charlie asked excitedly.  
  
"It's like a super fancy mall." Dean laughed.  
  
"If you run our of cash, I'm sure Moneybags Michael would get you anything you wanted." Charlie wiggled her eyebrows playfully.  
  
"Yeah but you know I'm not totally cool with that Charles. I mean I know he's marrying my mom and by tonight he'll be like....my dad, but I'm a little old for needing a dad now."  
  
Dean's father, John was killed in a car accident when Dean was two. He was too young to have any memories of John, which kind of made Dean sad. Dean knew it was strange to miss someone you had never known but he often did. He often wondered what John would have been like, and if he would have been as accepting as Mary had been when Dean came out as gay. He'd like to think so.  
  
Dean couldn't explain why he wasn't comfortable asking Michael for money. He was paying for the cruise. Had given Dean a credit card to use whenever he purchased anything onboard the ship:food, drinks, souvenirs, whatever he wanted. Michael was paying the bill when the trip was over. Even though Dean knew Michael could afford it, he didn't want to advantage of him.  
  
Dean and Charlie stepped on the the glass-enclosed elevator. Before the door could close, three guys about their age joined them. Dean punched the button for the floor-correction, the deck-his cabin was located.   
  
"The fancy deck," one of the guys said as he punched the deck two below Dean's. "First cruise?"  
  
Dean cast a glance over at Charlie and said "Yeah."  
  
"Us too." He smiled broadly and winked at Dean. "So far, so good."  
  
The elevator stopped. "See you around," he said as he and his friends got off.  
  
As soon as the doors closed, Charlie punched Dean's arm. "Dude! He was totally flirting with you!"   
  
Dean rolled his eyes. "No way, he was just being nice."

Charlie groaned. "No, he wasn't. Dean you should have flirted, given him your name. Shown a little more interest. If you want this to be the best time ever than you've got to stop being so shy around guys."  
  
"I will. As soon as we leave port," Dean insisted.   
  
Dean had dated a few guys in high school , but he'd never been serious about anyone. He'd spend most of his time studying, and been rewarded by graduating top of their class.  
  
Charlie, on the other hand, had always been comfortable around the ladies. Sometimes Dean wondered if being a lesbian was easier. Charlie also had a steady girlfriend-Gilda.  
  
Dean saw the cruise as his opportunity to break out of his shell, to meet guys and flirt and prepare himself for dating in college. He wanted to go places he'd never gone. And he didn't simply mean traveling to islands. He wanted to explore all the different facets of himself...and boys. He wanted to cut loose and do things he had never done.

The Cruise seemed the perfect place to try new things, because even if Dean made a fool of himself, he'd never see any of these people again so it didn't really matter if he made mistakes. He could be wild and crazy. He could be uninhibited, stretch the limits, take chances, complete his list of firsts. And no one would know that wild and crazy wasn't the real Dean Winchester.  
  
The elevator stopped. As they stepped out, Dean shifted his backpack on his shoulder and pulled one of his small wheeled suitcases behind him while Charlie dragged the other along with her duffel bag.  
  
With the plans to meet up later, Mary and Dean had parted ways right after boarding and checking in. Mary and Michael were staying in the honeymoon suite. Dean had their cabin number and could find them if they needed to, but he certainly didn't have any plans to search them out. It creeped him out to think about his mom on her honeymoon. No thank you!  
  
"It's too cool that you're going to have a cabin all to yourself," Charlie said. "You can do anything you want and your mom will never know!"  
  
Those were Dean's thoughts exactly. He had a feeling this new Cruising Dean was going to do more things that Mary definitely wouldn't approve of.  
  
"I think Michael made arrangements," Dean explained. More examples of his power to pill strings. From the research that he'd done on cruise ships, Michael and Mary were supposed to stay in a cabin beside his since he was eighteen. Twenty-one was the magical number for solo cruising. Whatever it was that Michael did Dean was glad he had done it.  
  
Since Mary had always worked, Dean had grown up fast and had acted responsibly as long as he could remember. He never got into trouble, always did his homework, and as soon as he'd gotten a driver's license, he'd taken on a part-time job at the mall movie theater. So he really didn't think he needed anyone to watch over him on the cruise ship.  
  
Michael apparently felt the same way. He had managed to accomplish the impossible, and that's all that mattered to Dean. With the ship being as large as it was , once his obligations regarding tonight were over. Dean might not see his mom and Michael for the rest of the cruise. It was all going to be perfect, except he did wish Charlie could come too.  
  
They reached the door to Dean's cabin and tapped his key card to the lock and cranked down the handle, and swung open the door.  
  
Dean's first thought was that he'd somehow mistakenly gotten the key to his Mom's suite. His second thought was that Michael had spared no expense to see that Dean was comfortable. The cabin had a king-sized bed, a large sitting area, and an awesome ocean view. Or at least it would be once they were surrounded by nothing but ocean.  
  
Dean pulled his suitcase into the cabin. "Holy crap, this place is huge!" 

"A small family could live in here!" Charlie said excitedly. "I thought rooms onboard ships were supposed to be tiny."  
  
"I'm sure there are some small rooms somewhere," Dean admitted. "Mine just isn't one of them."  
  
"I bet this cost a fortune."  
  
Dean rolled his eyes at Charlie as threw herself down on the bed.   
  
"You know I'm right, dude." Charlie continued. "It's like you're moving into a totally different world."  
  
Dean heard it in her voice, a world away from her. As soon as they returned home from the cruise, he and Mary would move into Michael's, and Dean would have a big bedroom there too.  
  
"You'll always be my best friend, Charlie." Dean said softly.  
  
"I know. I just wish I was going with you," she laughed. "I keep saying that don't I?"  
  
"Yeah, you do. And I keep saying I wish you were coming too."  
  
"Alas, I'm not. I need to accept it. But I will be taking full advantage of the pool for the few hours that I am here. Hey! Look at this! You've got a minibar! I'm totally taking a tiny bottle of wine." Charlie said excited once more.  
  
"Sure, go ahead. Drinking age is eighteen on the ship."  
  
"Awesome." She said, taking a bottle from the mini fridge.  
  
Dean shrugged off his backpack and walked across the cabin, unlocking the glass door and stepping out onto the veranda. The cool breeze off of the ocean caressed his face and brought a smile to his lips. This was going to be the best ten days of Dean's life. Glancing around Dean noticed that there was no one above his cabin but there were other balconies on either side of his, separated by waist high walls that offered a little privacy. He could sit out here with a good book and be in his own world.  
  
 _No!_ Dean thought to himself.  _That's what I'd do if I were at home. I need to be hanging around the pool, meeting guys, being completely different from my normal self._  
  
Charlie stepped out onto the veranda and snapped Dean out of his head.   
  
"Isn't this great?" He asked.  
  
"Absolutely" Charlie said as she handed Dean his own tiny bottle of wine. "I wanna make a toast." She raised her bottle. "Here's hoping you have the best time of your life!"   
  
"I'll drink to that!"  
  
They clinked their bottles and took a drink. This vacation was going to be perfect. Dean knew it without a doubt, because he was leaving nothing to chance. He'd made a list of all the things he needed to do in order to have a great time:  
  


  * Soak up the rays.
  * Shop until I drop
  * Drink margaritas by the pitcher.
  * Dance all night.
  * Climb a waterfall.
  * Snorkel.
  * Kiss a lot of cute guys.
  * Sleep with a guy for the first time.



**Author's Note:**

> Come yell at me on twitter @follow2thedark


End file.
